Heterocyclic compound and organic light-emitting device comprising same

ABSTRACT

An organic light-emitting device includes a heterocyclic compound represented by Formula 1 as a thermally activated delayed fluorescence dopant, where D 1  is a group represented by Formula 2 and Rw is selected from: —F, a cyano group, and a C 1 -C 20  alkyl group substituted with at least one —F:

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a National Phase Patent Application of InternationalPatent Application Number PCT/KR2018/010175, filed on Aug. 31, 2018,which claims priority to Korean Patent Application No. 10-2018-0069059,filed Jun. 15, 2018. The entire contents of both are incorporated hereinby reference.

FIELD

One or more embodiments of the present disclosure relate to aheterocyclic compound and an organic light-emitting device including thesame.

BACKGROUND

Organic light-emitting devices are self-emission devices that producefull-color images, and also have wide viewing angles, high contrastratios, short response times, and/or excellent characteristics in termsof brightness, driving voltage, and response speed, compared to devicesin the art.

The organic light-emitting device may include a first electrode disposedon a substrate, and a hole transport region, an emission layer, anelectron transport region, and a second electrode sequentially disposedon the first electrode. Holes provided from the first electrode may movetoward the emission layer through the hole transport region, andelectrons provided from the second electrode may move toward theemission layer through the electron transport region. Carriers (such asthe holes and electrons) recombine in the emission layer to produceexcitons. These excitons transition from an excited state to the groundstate, thereby generating light.

Description of Embodiments Technical Problem

One or more embodiments of the present disclosure are directed toward aheterocyclic compound and an organic light-emitting device including thesame.

Solution to Problem

One or more embodiments of the present disclosure provide a heterocycliccompound represented by Formula 1:

In Formulae 1 and 2,

A₁ is a C₅-C₆₀ carbocyclic group, a C₁-C₆₀ heterocyclic group, abiphenyl group, or a terphenyl group,

D₁ is a group represented by Formula 2,

n1 is an integer from 1 to 4,

L₁ is a single bond, a substituted or unsubstituted C₅-C₆₀ carbocyclicgroup, or a substituted or unsubstituted C₁-C₆₀ heterocyclic group,

a1 is an integer from 1 to 5,

R₁, R₃, R₄, R₅, R₇, R₈, and Ru are each independently selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an am idino group, a hydrazino group, a hydrazono group,a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryloxy group, a substituted or unsubstitutedC₁-C₆₀ heteroarylthio group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and—P(═O)(Q₁)(Q₂),

R₂ and R₆ are each independently selected from a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and—P(═O)(Q₁)(Q₂), wherein R₂ and R₆ are not substituted or unsubstitutedcarbazolyl groups,

b11 is an integer from 0 to 5,

R_(w) is selected from: —F, a cyano group, and a C₁-C₂₀ alkyl groupsubstituted with at least one —F;

a C₆-C₆₀ aryl group substituted with at least one selected from —F, acyano group, and a C₁-C₂₀ alkyl group substituted with at least one —F;

a C₁-C₆₀ heteroaryl group substituted with at least one selected from—F, a cyano group, and a C₁-C₂₀ alkyl group substituted with at leastone —F; and

a biphenyl group and a terphenyl group, each substituted with at leastone selected from —F, a cyano group, and a C₁-C₂₀ alkyl groupsubstituted with at least one —F,

b12 is an integer from 1 to 5, and

at least one substituent of the substituted C₅-C₆₀ carbocyclic group,the substituted C₁-C₆₀ heterocyclic group, the substituted C₁-C₆₀ alkylgroup, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substitutedC₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀ heterocycloalkyl group,the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, thesubstituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthio group,the substituted C₁-C₆₀ heteroaryl group, the substituted C₁-C₆₀heteroaryloxy group, the substituted C₁-C₆₀ heteroarylthio group, thesubstituted monovalent non-aromatic condensed polycyclic group, and thesubstituted monovalent non-aromatic condensed heteropolycyclic group isselected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆ oheteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆ o heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

wherein Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may eachindependently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group, and

* indicates a binding site to a neighboring atom.

One or more embodiments of the present disclosure provide an organiclight-emitting device including: a first electrode; a second electrodefacing the first electrode; and an organic layer located between thefirst electrode and the second electrode and including an emissionlayer, wherein the organic light-emitting device includes at least oneheterocyclic compound represented by Formula 1.

One or more embodiments of the present disclosure provide an organiclight-emitting device including: a first electrode; a second electrodefacing the first electrode; and an organic layer located between thefirst electrode and the second electrode and including an emissionlayer, wherein the organic layer includes at least one heterocycliccompound represented by Formula 1.

Advantageous Effects of Disclosure

The organic light-emitting device including the heterocyclic compoundmay have low driving voltage, high efficiency, and/or a long lifespan.

BRIEF DESCRIPTION OF DRAWINGS

FIGS. 1 to 4 are each a schematic view of a structure of an organiclight-emitting device according to an embodiment.

DETAILED DESCRIPTION

Hereinafter, the present disclosure will be described in more detail.

One or more embodiments of the present disclosure provide a heterocycliccompound represented by Formula 1.

In Formula 1, A₁ may be a C₅-C₆₀ carbocyclic group, a C₁-C₆₀heterocyclic group, a biphenyl group, or a terphenyl group.

The term “biphenyl group” as used herein refers to a divalent groupincluding two directly linked benzene groups. The biphenyl group may berepresented by the following formula:

In the above formula, * and *′ each indicates a binding site to aneighboring atom.

The term “terphenyl group” as used herein refers to a divalent groupincluding three directly linked benzene groups. The terphenyl group maybe represented by the following formula.

In the above formula, * and *′ each indicates a binding site to aneighboring atom.

In one embodiment, A₁ in Formula 1 may be selected from a benzene group,an indene group, a naphthalene group, an anthracene group, a fluorenegroup, a phenanthrene group, a triphenylene group, a pyrene group, achrysene group, a naphthacene group, a pyrrole group, an imidazolegroup, a pyrazole group, a pyridine group, a pyrimidine group, apyrazine group, a pyridazine group, an indole group, an isoindole group,an indazole group, a quinoline group, an isoquinoline group, abenzoquinoline group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a carbazole group, aphenanthridine group, an acridine group, a phenanthroline group, aphenazine group, a benzimidazole group, a furan group, a benzofurangroup, a thiophene group, a benzothiophene group, a thiazole group, anisothiazole group, a benzothiazole group, an isooxazole group, anoxazole group, a triazole group, an oxadiazole group, a triazine group,a benzoxazole group, a dibenzofuran group, a dibenzothiophene group, abenzocarbazole group, a dibenzocarbazole group, a biphenyl group, and aterphenyl group.

In one embodiment, A₁ may be selected from a benzene group, a biphenylgroup, and a terphenyl group.

In Formula 1, D₁ may be a group represented by Formula 2.

In Formula 1, n1 may be an integer from 1 to 4. n1 indicates the numberof D₁ substituents, wherein when n1 is 2 or more, two or more D₁(s) maybe identical to or different from each other.

In one embodiment, n1 may be 2 or 3.

In one embodiment, n1 may be 2 or 3, and the n1 D₁(s) may be identicalto each other.

In Formula 2, Li may be a single bond, a substituted or unsubstitutedC₅-C₆₀ carbocyclic group, or a substituted or unsubstituted C₁-C₆₀heterocyclic group.

In one embodiment, Li may be selected from: a single bond, a benzenegroup, a pentalene group, an indene group, a naphthalene group, anazulene group, a heptalene group, an indacene group, an acenaphthalenegroup, a fluorene group, a spiro-bifluorene group, a benzofluorenegroup, a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphenylene group, a hexacene group, a pyrrole group, an imidazolegroup, a pyrazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an isoindole group, an indolegroup, an indazole group, a purine group, a quinoline group, anisoquinoline group, a benzoquinoline group, a phthalazine group, anaphthyridine group, a quinoxaline group, a quinazoline group, acinnoline group, a carbazole group, a phenanthridine group, an acridinegroup, a phenanthroline group, a phenazine group, a benzoxazole group, abenzimidazole group, a furan group, a benzofuran group, a thiophenegroup, a benzothiophene group, a thiazole group, an isothiazole group, abenzothiazole group, an isoxazole group, an oxazole group, a triazolegroup, a tetrazole group, an oxadiazole group, a triazine group, abenzoxazole group, a dibenzofuran group, a dibenzothiophene group, abenzocarbazole group, and a dibenzocarbazole group; and

a benzene group, a pentalene group, an indene group, a naphthalenegroup, an azulene group, a heptalene group, an indacene group, anacenaphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a phenalene group, a phenanthrene group, ananthracene group, a fluoranthene group, a triphenylene group, a pyrenegroup, a chrysene group, a naphthacene group, a picene group, a perylenegroup, a pentaphenylene group, a hexacene group, a pyrrole group, animidazole group, a pyrazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an isoindole group, an indolegroup, an indazole group, a purine group, a quinoline group, anisoquinoline group, a benzoquinoline group, a phthalazine group, anaphthyridine group, a quinoxaline group, a quinazoline group, acinnoline group, a carbazole group, a phenanthridine group, an acridinegroup, a phenanthroline group, a phenazine group, a benzoxazole group, abenzimidazole group, a furan group, a benzofuran group, a thiophenegroup, a benzothiophene group, a thiazole group, an isothiazole group, abenzothiazole group, an isoxazole group, an oxazole group, a triazolegroup, a tetrazole group, an oxadiazole group, a triazine group, abenzoxazole group, a dibenzofuran group, a dibenzothiophene group, abenzocarbazole group, and a dibenzocarbazole group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a C₆-C₂₀ aryl group, a C₁-C₂₀ heteroaryl group,—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), and—S(═O)₂(Q₃₁),

wherein Q₃₁ to Q₃₃ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazino group, a hydrazonogroup,

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

In one embodiment, Li may be selected from a single bond and groupsrepresented by Formulae 3-1 to 3-46:

In Formulae 3-1 to 3-46,

Y₁ may be O, S, C(Z₃)(Z₄), N(Z₅), or Si(Z₆)(Z₇),

Z₁ to Z₇ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a biphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a spiro-fluorene-benzofluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a naphthyridinyl group, a quinoxalinyl group, a quinazolinylgroup, a carbazolyl group, a phenanthridinyl group, an acridinyl group,a phenanthrolinyl group, a phenazinyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃),—N(Q₃₁)(Q₃₂), and —B(Q₃₁)(Q₃₂),

d2 may be an integer from 1 to 2,

d3 may be an integer from 1 to 3,

d4 may be an integer from 1 to 4,

d5 may be an integer from 1 to 5,

d6 may be an integer from 1 to 6,

d8 may be an integer from 1 to 8, and

Q₃₁ to Q₃₃ may each independently be selected from hydrogen, deuterium,a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a C₆-C₆₀ aryl group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, a monovalent non-aromatic condensed heteropolycyclic group, abiphenyl group, and a terphenyl group.

In Formulae 3-1 to 3-46, * and *′ each indicate a binding site to aneighboring atom.

In one or more embodiments, Li may be a single bond, but embodiments ofthe present disclosure are not limited thereto.

In Formula 2, a1 may be an integer from 1 to 5. a1 indicates the numberof Li, wherein when a1 is 2 or more, two or more Li(s) may be identicalto or different from each other.

In Formula 2, R₁, R₃, R₄, R₅, R₇, R₈, and R₁₁ may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryloxy group, a substituted or unsubstitutedC₁-C₆₀ heteroarylthio group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and—P(═O)(Q₁)(Q₂).

In Formula 1, b11 may be an integer from 0 to 5. b11 indicates thenumber of R₁₁, wherein when b11 is 2 or more, two or more R₁₁(s) may beidentical to or different from each other.

In one embodiment, R₁, R₃, R₄, R₅, R₇, and R₈ may each be hydrogen.

In Formula 2, R₂ and R₆ may each independently be selected from asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryloxy group, a substituted or unsubstitutedC₁-C₆₀ heteroarylthio group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and—P(═O)(Q₁)(Q₂).

In some embodiments, however, R₂ and R₆ are not substituted orunsubstituted carbazolyl groups.

In one embodiment, R₂ and R₆ may each independently be selected from: aC₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, aphenyl group, and a biphenyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a perylenyl group, apentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an indolyl group, an isoindolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, an isoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, aquinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, abenzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group,a triazolyl group, a tetrazolyl group, a thiadiazolyl group, anoxadiazolyl group, and a triazinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a perylenyl group, apentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an indolyl group, an isoindolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, an isoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, aquinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, abenzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group,a triazolyl group, a tetrazolyl group, a thiadiazolyl group, anoxadiazolyl group, and a triazinyl group, each substituted with at leastone selected from deuterium, —F, —Cl, —Br, —I, a cyano group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, an indacenylgroup, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenylgroup, a furanyl group, a silolyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, abenzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinylgroup, a cinnolinyl group, a phenanthridinyl group, an acridinyl group,a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, a benzosilolyl group, abenzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, abenzoisoxazolyl group, a triazolyl group, a tetrazolyl group, athiadiazolyl group, an oxadiazolyl group, a triazinyl group,—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), and —B(Q₃₁)(Q₃₂); and —Si(Q₁)(Q₂)(Q₃),—N(Q₁)(Q₂), and —B(Q₁)(Q₂),

wherein Q₁ to Q₃ and Q₃₁ to Q₃₃ may each independently be selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

In one embodiment, R₂ and R₆ may each independently be selected from: amethyl group, an ethyl group, an n-propyl group, an isopropyl group, ann-butyl group, an isobutyl group, a sec-butyl group, and a tert-butylgroup;

a methyl group, an ethyl group, an n-propyl group, an isopropyl group,an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butylgroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, and a cyano group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, and a triazinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, and a triazinyl group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenylgroup, a pyrenyl group, a chrysenyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinylgroup, an isoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a carbazolyl group, a triazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃),—N(Q₃₁)(Q₃₂), and —B(Q₃₁)(Q₃₂); and

—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), and —B(Q₁)(Q₂),

wherein Q₁ to Q₃ and Q₃₁ to Q₃₃ may each independently be selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

In one or more embodiments, R₂ and R₆ may each independently be selectedfrom: a methyl group, an ethyl group, an n-propyl group, an isopropylgroup, an n-butyl group, an isobutyl group, a sec-butyl group, and atert-butyl group;

a phenyl group, a biphenyl group, a terphenyl group, and a naphthylgroup; and

a phenyl group and a naphthyl group, each substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a cyano group, a methylgroup, an ethyl group, an n-propyl group, an isopropyl group, an n-butylgroup, an isobutyl group, a sec-butyl group, a tert-butyl group, aphenyl group, a naphthyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), and—B(Q₃₁)(Q₃₂),

wherein Q₃₁ to Q₃₃ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a cyano group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, a biphenyl group,and a terphenyl group.

In Formula 1, R_(w) may be selected from: —F, a cyano group, and aC₁-C₂₀ alkyl group substituted with at least one —F;

a C₆-C₆₀ aryl group substituted with at least one selected from —F, acyano group, and a C₁-C₂₀ alkyl group substituted with at least one —F;

a C₁-C₆₀ heteroaryl group substituted with at least one selected from—F, a cyano group, and a C₁-C₂₀ alkyl group substituted with at leastone —F; and

a biphenyl group and a terphenyl group, each substituted with at leastone selected from —F, a cyano group, and a C₁-C₂₀ alkyl groupsubstituted with at least one —F.

In one embodiment, R_(w) may be selected from: —F, a cyano group, and aC₁-C₂₀ alkyl group substituted with at least one —F; and

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, an indacenylgroup, an acenaphthyl group, a fluorenyl group, a phenalenyl group, aphenanthrenyl group, a fluoranthenyl group, a triphenylenyl group, aperylenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an indolyl group, an isoindolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, an isoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, aquinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, aphenazinyl group, a benzofuranyl group, a benzothiophenyl group, abenzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, abenzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, atetrazolyl group, a thiadiazolyl group, and an oxadiazolyl group, eachsubstituted with at least one selected from —F, a cyano group, and aC₁-C₂₀ alkyl group substituted with at least one —F.

In one embodiment, R_(w) may be selected from: —F, a cyano group, and—CF₃; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, apyridinyl group, a pyrazinyl group, and a pyrimidinyl group, eachsubstituted with at least one selected from —F, a cyano group, and —CF₃.

In one or more embodiments, R_(w) may be selected from: —F, a cyanogroup, and —CF₃; and

a phenyl group substituted with at least one selected from —F, a cyanogroup, and —CF₃.

In one or more embodiments, R_(w) may be selected from —F, a cyanogroup, —CF₃, and groups represented by Formulae 5-1 to 5-7:

In Formulae 5-1 to 5-7,

* indicates a binding site to a neighboring atom.

In Formula 1, b12 may be an integer from 1 to 5. b12 indicates thenumber of R_(w), wherein when b12 is 2 or more, two or more R_(w)(s) maybe identical to or different from each other.

In one embodiment, b12 may be 1, 2, 3, or 4.

In one embodiment, the heterocyclic compound may be represented by anyone of Formulae 1A-1 to 1A-4 and 1B-1 to 1B-9:

In Formulae 1A-1 to 1A-4 and 1B-1 to 1B-9,

Rug and R_(w) are the same as described in connection with Formula 1,

R₁₂ and R₁₃ are the same as described in connection with Ru in Formula1,

R_(wa) and R_(wb) are the same as described in connection with R_(w) inFormula 1,

D_(1a) to D₁ are the same as described in connection with D₁ in Formula1,

b13 is 0, 1, 2, or 3, b14 is 1, 2, 3, or 4, and the sum of b13 and b14is 4,

b15 is 0, 1, 2, or 3, b16 is 1, 2, 3, or 4, and the sum of b15 and b16is 4, and

b17 is 0, 1, or 2, b18 is 1, 2, or 3, and the sum of b17 and b18 is 3.

In one embodiment, in Formulae 1A-1 to 1A-4 and 1B-1 to 1B-9,

R_(w), R_(wa), and R_(wb) may each independently be selected from: —F, acyano group, and —CF₃; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, apyridinyl group, a pyrazinyl group, and a pyrimidinyl group, eachsubstituted with at least one selected from —F, a cyano group, and —CF₃.

In one embodiment, the heterocyclic compound may be represented by anyone of Formulae 1A-2-1 to 1A-2-6, 1A-4-1, 1B-1-1 to 1B-1-2, 1B-4-1 to1B-4-3, and 1B-7-1 to 1B-7-3:

In Formulae 1A-2-1 to 1A-2-6, 1A-4-1, 1B-1-1 to 1B-1-2, 1B-4-1 to1B-4-3, and 1B-7-1 to 1B-7-3,

R₁₁ and R_(w) are the same as described in connection with Formula 1,

R₁₂ and R₁₃ are the same as described in connection with Ru in Formula1,

R_(wa) to R_(wd) are the same as described in connection with R_(w) inFormula 1,

D_(1a) to D_(1c) are the same as described in connection with D₁ inFormula 1,

b13 is 0, 1, 2, or 3, and

b17 is 0, 1, or 2.

In one embodiment, in Formulae 1A-2-1 to 1A-2-6, 1A-4-1, 1B-1-1 to1B-1-2, 1B-4-1 to 1B-4-3, and 1B-7-1 to 1B-7-3,

R_(w) and R_(wa) to R_(wd) may each independently be selected from: —F,a cyano group, and —CF₃; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, apyridinyl group, a pyrazinyl group, and a pyrimidinyl group, eachsubstituted with at least one selected from —F, a cyano group, and —CF₃.

In one or more embodiments, the heterocyclic compound may be representedby any one of Formulae HA-2-1 to HA-2-6, HA-4-1, HB-1-1 to HB-1-2,HB-4-1 to HB-4-3, and HB-7-1 to HB-7-3:

In Formulae HA-2-1 to HA-2-6, HA-4-1, HB-1-1 to HB-1-2, HB-4-1 toHB-4-3, and HB-7-1 to HB-7-3,

R₁₁ and R_(w) are the same as described in connection with Formula 1,

R_(wa) to R_(wd) are the same as described in connection with R_(w) inFormula 1, and

D_(1a) to D_(1c) are the same as described in connection with D₁ inFormula 1.

In one embodiment, in Formulae HA-2-1 to HA-2-6, HA-4-1, HB-1-1 toHB-1-2, HB-4-1 to HB-4-3, and HB-7-1 to HB-7-3,

R_(w) and R_(wa) to R_(wd) may each independently be selected from: —F,a cyano group, and —CF₃; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, apyridinyl group, a pyrazinyl group, and a pyrimidinyl group, eachsubstituted with at least one selected from —F, a cyano group, and —CF₃.

In one embodiment, the heterocyclic compound may have a symmetricstructure (the heterocyclic compound may have at least one plane ofsymmetry).

In one embodiment, the heterocyclic compound may be selected fromCompounds 1 to 126, but embodiments of the present disclosure are notlimited thereto.

The heterocyclic compound includes a substituent having properties of anelectron withdrawing group (EWG) as well as a substituent havingproperties of an electron donating group (EDG), and when thesesubstituents are introduced in suitable positions, an energy differencebetween a singlet state and a triplet state of the compound may beappropriately or suitably adjusted. Accordingly, the heterocycliccompound may exhibit thermally activated delayed fluorescence (TADF).

The following Equation describes a suitable relationship between asinglet energy and a triplet energy of the heterocyclic compound:ΔE_(st)=S1−T1<0.3 eV

The heterocyclic compound includes a structure represented by Formula 1.In particular, because the compound includes an EWG and an EDG, chargetransfer within the molecule may be easily achieved. In addition,orbital overlap in the molecule may be efficiently or suitably blockeddue to steric hindrance between the EWG and the EDG in the structure.Accordingly, ΔE_(st) may be extremely or suitably low while a singletand a triplet state of the molecule do not overlap. Accordingly, reverseintersystem crossing from a triplet excited state to a singlet excitedstate may occur via thermal activation, even at room temperature,resulting in delayed fluorescence. Because excitons in the triplet stateare used for emission, luminescence efficiency may be improved.Theoretically, ΔE_(st) and oscillator strength generally have atrade-off relationship, such that the smaller the ΔE_(st), the lower theluminescence efficiency. However, in a case of a compound satisfyingFormula 1, ΔE_(st) may be suppressed to a low value, and the structuremay simultaneously have a high oscillator strength, such that theheterocyclic compound represented by Formula 1 may have relatively highphotoluminescence quantum yield (PLQY).

In the group represented by Formula 2, carbons 2 and 6 of a carbazolegroup may be substituted with a group (substituent) other than hydrogen.When a compound including a carbazole group substituted on carbons 3 and6 is instead used in an emission layer of an organic light-emittingdevice, the compound may have a maximum emission wavelength on thehigher end of 400 nm, for example, greater than 470 nm. Meanwhile, acompound including a carbazole group substituted on carbons 2 and 7 mayhave a shortened maximum emission wavelength of less than 450 nm. Incontrast, because a group represented by Formula 2 includes asubstituent on carbons 2 and 6 of carbazole, the heterocyclic compoundrepresented by Formula 1 may be to emit deep-blue light having a maximumemission wavelength of 450 nm to 470 nm.

Furthermore, because the heterocyclic compound has relatively highcharge (hole or electron) transport ability, an exciton formation ratioin an emission layer of an organic light-emitting device using theheterocyclic compound represented by Formula 1 may be improved.Accordingly, the organic light-emitting device may have low drivingvoltage, high efficiency, long lifespan, and/or high maximum quantumefficiency.

A synthesis method for the heterocyclic compound represented by Formula1 would be understood by those of ordinary skill in the art by referringto the following examples.

At least one of the heterocyclic compound represented by Formula 1 maybe used between a pair of electrodes of an organic light-emittingdevice. In one or more embodiments, the heterocyclic compound may beincluded in at least one of a hole transport region, an electrontransport region, and an emission layer. In one or more embodiments, theheterocyclic compound represented by Formula 1 may be used as a materialfor a capping layer located outside a pair of electrodes of an organiclight-emitting device.

Accordingly, provided is an organic light-emitting device including: afirst electrode; a second electrode facing the first electrode; and anorganic layer located between the first electrode and the secondelectrode and including an emission layer, wherein the organiclight-emitting device includes at least one heterocyclic compoundrepresented by Formula 1.

In one embodiment, provided is an organic light-emitting deviceincluding: a first electrode; a second electrode facing the firstelectrode; and an organic layer located between the first electrode andthe second electrode and including an emission layer, wherein theorganic layer includes at least one heterocyclic compound represented byFormula 1.

The expression “(an organic layer) includes at least one heterocycliccompound” as used herein may include a case in which “(an organic layer)includes identical heterocyclic compounds represented by Formula 1” (onesame heterocyclic compound) and a case in which “(an organic layer)includes two or more different heterocyclic compounds represented byFormula 1”.

In one or more embodiments, the organic layer may include, as theheterocyclic compound, only Compound 1. In this regard, Compound 1 mayexist (be included) only in the emission layer of the organiclight-emitting device. In one or more embodiments, the organic layer mayinclude, as the heterocyclic compound, Compound 1 and Compound 2. Inthis regard, Compound 1 and Compound 2 may exist in the same layer (forexample, Compound 1 and Compound 2 may both (simultaneously) exist in anemission layer), or in different layers (for example, Compound 1 mayexist in an emission layer and Compound 2 may exist in an electrontransport layer).

In one embodiment, the first electrode is an anode, the second electrodeis a cathode, and the organic layer further includes a hole transportregion between the first electrode and the emission layer and anelectron transport region between the emission layer and the secondelectrode; the hole transport region includes a hole injection layer, ahole transport layer, an emission auxiliary layer, an electron blockinglayer, or any combination thereof; and the electron transport regionincludes a hole blocking layer, an electron transport layer, an electroninjection layer, or any combination thereof.

In one embodiment, the hole transport region may include a holetransport layer,

the hole transport layer may include a first hole transport layer and asecond hole transport layer, and

a material included in the first hole transport layer and a materialincluded in the second hole transport layer may be identical to ordifferent from each other.

In one embodiment, the emission layer of the organic light-emittingdevice may include the heterocyclic compound.

In one or more embodiments, the emission layer may consist of theheterocyclic compound, or in some embodiments, the emission layer mayfurther include a host, and an amount of the heterocyclic compound maybe 0.1 parts by weight to 50 parts by weight based on 100 parts byweight of the emission layer.

In one or more embodiments, the emission layer includes the heterocycliccompound and a host, and the heterocyclic compound may be or act as adopant.

In one or more embodiments, the heterocyclic compound included in theemission layer is a thermally activated delayed fluorescence emitter(TADF emitter), and the emission layer may be to emit delayedfluorescence.

The host in the emission layer may include at least one of ananthracene-based compound, a pyrene-based compound, aspiro-bifluorene-based compound, a carbazole-based compound, abenzimidazole-based compound, a phosphine oxide-based compound, adibenzofuran-based compound, a silicon-based compound, and atriazine-based compound, but embodiments of the present disclosure arenot limited thereto.

In one embodiment, the emission layer includes the heterocycliccompound, and the emission layer may be to emit blue light having amaximum emission wavelength of 450 nm to 470 nm.

In one embodiment, the electron transport region of the organiclight-emitting device may include at least one of a phosphineoxide-based compound and a benzimidazole-based compound, and

may further include an alkali metal, an alkaline earth metal, a rareearth metal, an alkali metal compound, an alkaline earth metal compound,a rare earth metal compound, an alkali metal complex, an alkaline earthmetal complex, a rare earth metal complex, or any combination thereof.

The term “organic layer” as used herein refers to a single layer and/orall layers between the first electrode and the second electrode of theorganic light-emitting device. A material included in “the organiclayer” is not limited to an organic material. [Description of FIG. 1]

FIG. 1 is a schematic cross-sectional view of an organic light-emittingdevice 10 according to an embodiment of the present disclosure. Theorganic light-emitting device 10 includes a first electrode 110, anorganic layer 150, and a second electrode 190.

Hereinafter, a structure of the organic light-emitting device 10according to an embodiment of the present disclosure and a method ofmanufacturing the organic light-emitting device 10 according to anembodiment of the present disclosure will be described in connectionwith FIG. 1.

[First Electrode 110]

In FIG. 1, a substrate may be additionally disposed under the firstelectrode 110 or above the second electrode 190. The substrate may be aglass substrate and/or a plastic substrate, each having excellentmechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and/or water resistance.

The first electrode 110 may be formed by depositing and/or sputtering amaterial for forming the first electrode 110 on the substrate. When thefirst electrode 110 is an anode, a material for forming the firstelectrode 110 may be selected from materials with a high work functionto facilitate hole injection.

The first electrode 110 may be a reflective electrode, asemi-transmissive electrode, or a transmissive electrode. When the firstelectrode 110 is a transmissive electrode, a material for forming thefirst electrode 110 may be selected from indium tin oxide (ITO), indiumzinc oxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), and anycombination thereof, but embodiments of the present disclosure are notlimited thereto. In one or more embodiments, when the first electrode110 is a semi-transmissive electrode or a reflective electrode, amaterial for forming the first electrode 110 may be selected frommagnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li),calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), andany combination thereof, but embodiments of the present disclosure arenot limited thereto.

The first electrode 110 may have a single-layered structure or amulti-layered structure including two or more layers. In one or moreembodiments, the first electrode 110 may have a three-layered structureof ITO/Ag/ITO, but embodiments of the present disclosure are not limitedthereto.

[Organic Layer 150]

The organic layer 150 is located on the first electrode 110. The organiclayer 150 includes an emission layer.

The organic layer 150 may further include a hole transport regionbetween the first electrode 110 and the emission layer and an electrontransport region between the emission layer and the second electrode190.

[Hole Transport Region in Organic Layer 150]

The hole transport region may have i) a single-layered structureincluding (or consisting of) a single material, ii) a single-layeredstructure including (or consisting of) a plurality of differentmaterials, or iii) a multi-layered structure having a plurality oflayers including (or consisting of) a plurality of different materials.

The hole transport region may include at least one layer selected from ahole injection layer, a hole transport layer, an emission auxiliarylayer, and an electron blocking layer.

In one or more embodiments, the hole transport region may have asingle-layered structure including (or consisting of) a plurality ofdifferent materials, or a multi-layered structure having a holeinjection layer/hole transport layer, a hole injection layer/holetransport layer/emission auxiliary layer, a hole injectionlayer/emission auxiliary layer structure, a hole transportlayer/emission auxiliary layer, or a hole injection layer/hole transportlayer/electron blocking layer, wherein the constituting layers of eachstructure are sequentially stacked from the first electrode 110 in thisstated order, but embodiments of the present disclosure are not limitedthereto.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB(NPD), p-NPB, TPD, spiro-TPD, spiro-NPB,methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzene sulfonic acid (PANI/DBSA),poly(3,4-ethylene dioxythiophene)/poly(4-styrene sulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201, and acompound represented by Formula 202:

In Formulae 201 and 202,

L₂₀₁ to L₂₀₄ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

L₂₀₅ may be selected from *—O—*′, *—S—*′, *—N(Q₂₀₁)-*′, a substituted orunsubstituted C₁-C₂₀ alkylene group, a substituted or unsubstitutedC₂-C₂₀ alkenylene group, a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xa1 to xa4 may each independently be an integer from 0 to 3,

xa5 may be an integer from 1 to 10, and

R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independently be selected from asubstituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted orunsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In one or more embodiments, in Formula 202, R₂₀₁ and R₂₀₂ may optionallybe linked to each other via a single bond, a dimethyl-methylene group,or a diphenyl-methylene group, and R₂₀₃ and R₂₀₄ may optionally belinked to each other via a single bond, a dimethyl-methylene group, or adiphenyl-methylene group.

In one embodiment, in Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may each independently be selected from:

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an am idino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂),

wherein Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group.

In one or more embodiments, xa1 to xa4 may each independently be 0, 1,or 2.

In one or more embodiments, xa5 may be 1, 2, 3, or 4.

In one or more embodiments, R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independentlybe selected from a phenyl group, a biphenyl group, a terphenyl group, apentalenyl group, an indenyl group, a naphthyl group, an azulenyl group,a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂),

wherein Q₃₁ to Q₃₃ are the same as described above.

In one or more embodiments, at least one of R₂₀₁ to R₂₀₃ in Formula 201may each independently be selected from:

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a phenyl group substituted with a C₁-C₁₀ alkylgroup, a phenyl group substituted with —F, a naphthyl group, a fluorenylgroup, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, in Formula 202, i) R₂₀₁ and R₂₀₂ may belinked to each other via a single bond, and/or ii) R₂₀₃ and R₂₀₄ may belinked to each other via a single bond.

In one or more embodiments, R₂₀₁ to R₂₀₄ in Formula 202 may be selectedfrom:

a carbazolyl group; and

a carbazolyl group substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, acarbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, the compound represented by Formula 201 maybe represented by Formula 201A:

In one or more embodiments, the compound represented by Formula 201 maybe represented by Formula 201A(1), but embodiments of the presentdisclosure are not limited thereto:

In one or more embodiments, the compound represented by Formula 201 maybe represented by Formula 201A-1, but embodiments of the presentdisclosure are not limited thereto:

In one or more embodiments, the compound represented by Formula 202 maybe represented by Formula 202A:

In one or more embodiments, the compound represented by Formula 202 maybe represented by Formula 202A-1:

In Formulae 201A, 201A(1), 201A-1, 202A, and 202A-1,

L₂₀₁ to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂ to R₂₀₄ are the same asdescribed above,

R₂₁₁ and R₂₁₂ are the same as described in connection with R₂₀₃, and

R₂₁₃ to R₂₁₇ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an am idino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group.

The hole transport region may include at least one compound selectedfrom Compounds HT1 to HT39, but compounds to be included in the holetransport region are not limited thereto:

A thickness of the hole transport region may be about 100Å to about10,000 Å, for example, about 100Å to about 1,000 Å. When the holetransport region includes at least one of a hole injection layer and ahole transport layer, a thickness of the hole injection layer may beabout 100Å to about 9,000 Å, for example, about 100Å to about 1,000 Å,and a thickness of the hole transport layer may be about 50 Å to about2,000 Å, for example, about 100Å to about 1,500 Å. When the thicknessesof the hole transport region, the hole injection layer, and the holetransport layer are within these ranges, satisfactory hole transportingcharacteristics may be obtained without a substantial increase indriving voltage.

The emission auxiliary layer may increase the light-emission efficiencyof the device by compensating for an optical resonance distance of thewavelength of light emitted by an emission layer, and the electronblocking layer may block or reduce the flow of electrons from anelectron transport region. The emission auxiliary layer and the electronblocking layer may include the materials as described above.

[p-Dopant]

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may behomogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant.

In one embodiment, a lowest unoccupied molecular orbital (LUMO) energylevel of the p-dopant may be −3.5 eV or less.

The p-dopant may include at least one selected from a quinonederivative, a metal oxide, and a cyano group-containing compound, butembodiments of the present disclosure are not limited thereto.

In one or more embodiments, the p-dopant may include at least oneselected from:

a quinone derivative (such as tetracyanoquinodimethane (TCNQ) and/or2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ));

a metal oxide (such as tungsten oxide and/or molybdenum oxide);

1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and

a compound represented by Formula 221,

but embodiments of the present disclosure are not limited thereto:

In Formula 221,

R₂₂₁ to R₂₂₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, and at least one of R₂₂₁to R₂₂₃ may have at least one substituent selected from a cyano group,—F, —Cl, —Br, —I, a C₁-C₂₀ alkyl group substituted with —F, a C₁-C₂₀alkyl group substituted with —CI, a C₁-C₂₀ alkyl group substituted withBr, and a C₁-C₂₀ alkyl group substituted with —I.

[Emission Layer in Organic Layer 150]

When the organic light-emitting device 10 is a full-color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, or a blue emission layer,according to a sub-pixel. In one or more embodiments, the emission layermay have a stacked structure of two or more layers selected from a redemission layer, a green emission layer, and a blue emission layer, inwhich the two or more layers contact each other or are separated fromeach other to emit white light. In one or more embodiments, the emissionlayer may include two or more materials selected from a redlight-emitting material, a green light-emitting material, and a bluelight-emitting material, where the two or more materials are mixed witheach other in a single layer to emit white light.

The emission layer may include a host and a dopant. The dopant mayinclude at least one of a phosphorescent dopant and a fluorescentdopant.

An amount of the dopant in the emission layer may be, based on about 100parts by weight of the host, about 0.01 parts by weight to about 15parts by weight, but embodiments of the present disclosure are notlimited thereto.

A thickness of the emission layer may be about 100Å to about 1,000 Å,for example, about 200Å to about 600 Å. When the thickness of theemission layer is within this range, excellent light-emissioncharacteristics may be obtained without a substantial increase indriving voltage.

[Host in Emission Layer]

The host may include a compound represented by Formula 301:

[Ar₃₀₁]_(xb11)-[(L₃₀₁)_(xb1)-R₃₀₁]_(xb21).  <Formula 301>

In Formula 301,

Ar₃₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xb11 may be 1, 2, or 3,

L₃₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xb1 may be an integer from 0 to 5,

R₃₀₁ may be selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂),—B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), and —P(═O)(Q₃₀₁)(Q₃₀₂), and

xb21 may be an integer from 1 to 5,

wherein Q₃₀₁ to Q₃₀₃ may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group, but embodiments of the presentdisclosure are not limited thereto.

In one embodiment, Ar₃₀₁ in Formula 301 may be selected from:

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup; and

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

wherein Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group, but embodiments of the presentdisclosure are not limited thereto.

When xb11 in Formula 301 is 2 or more, two or more Ar₃₀₁(s) may belinked to each other via a single bond.

In one embodiment, the compound represented by Formula 301 may berepresented by Formula 301-1 or Formula 301-2:

In Formulae 301-1 and 301-2,

A₃₀₁ to A₃₀₄ may each independently be selected from benzene,naphthalene, phenanthrene, fluoranthene, triphenylene, pyrene, chrysene,pyridine, pyrimidine, indene, fluorene, spiro-bifluorene, benzofluorene,dibenzofluorene, indole, carbazole, benzocarbazole, dibenzocarbazole,furan, benzofuran, dibenzofuran, naphthofuran, benzonaphthofuran,dinaphthofuran, thiophene, benzothiophene, dibenzothiophene,naphthothiophene, benzonaphthothiophene, and dinaphthothiophene,

X₃₀₁ may be O, S₇ or N-[(L₃₀₄)_(xb4)-R₃₀₄],

R₃₁₁ to R₃₁₄ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

xb22 and xb23 may each independently be 0, 1, or 2,

L₃₀₁, xb1, R₃₀₁, and Q₃₁ to Q₃₃ are the same as described above,

L₃₀₂ to L₃₀₄ are each independently the same as described in connectionwith L₃₀₁,

xb2 to xb4 may each independently be the same as described in connectionwith xb1₇ and

R₃₀₂ to R₃₀₄ are each independently the same as described in connectionwith R₃₀₁.

In one or more embodiments, L₃₀₁ to L₃₀₄ in Formulae 301, 301-1, and301-2 may each independently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an am idino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, an azacarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

wherein Q₃₁ to Q₃₃ are the same as described above.

In one or more embodiments, R₃₀₁ to R₃₀₄ in Formulae 301, 301-1, and301-2 may each independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —C, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

wherein Q₃₁ to Q₃₃ are the same as described above.

In one or more embodiments, the host may include an alkaline earth metalcomplex. In one or more embodiments, the host may be selected from a Becomplex (for example, Compound H55) and an Mg complex. In someembodiments, the host may be a Zn complex.

The host may include at least one selected from9,10-di(2-naphthyl)anthracene (ADN),2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN),4,4′-bis(N-carbazolyI)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene(mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and at least one selectedfrom Compounds H1 to H55, but embodiments of the present disclosure arenot limited thereto:

[Phosphorescent Dopant Included in Emission Layer in Organic Layer 150]

The phosphorescent dopant may include an organometallic complexrepresented by Formula 401:

M(L₄₀₁)_(xc1)(L₄₀₂)^(xc2)   <Formula 401>

In Formulae 401 and 402,

M may be selected from iridium (Ir), platinum (Pt), palladium (Pd),osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu),terbium (Tb), rhodium (Rh), and thulium (Tm),

L₄₀₁ may be selected from ligands represented by Formula 402, and xc1may be 1, 2, or 3, wherein when xc1 is 2 or more, two or more of L₄₀₁(s)may be identical to or different from each other,

L₄₀₂ may be an organic ligand, and xc2 may be an integer from 0 to 4,wherein when xc2 is 2 or more, two or more of L₄₀₂(s) may be identicalto or different from each other,

X₄₀₁ to X₄₀₄ may each independently be nitrogen or carbon,

X₄₀₁ and X₄₀₃ may be linked via a single bond or a double bond, and X₄₀₂and X₄₀₄ may be linked via a single bond or a double bond,

A₄₀₁ and A₄₀₂ may each independently be a C₅-C₆₀ carbocyclic group or aC₁-C₆₀ heterocyclic group,

X₄₀₅ may be a single bond, *—O-′, *—S—*′, *—C(═O)—*′, *—N(Q₄₁₁)-*′,*—C(Q₄₁₁)(Q₄₁₂)-*′, *—C(Q₄₁₁)═C(Q₄₁₂)-′, *—C(Q₄₁₁)=*′, or *═C(Q₄₁₁)=*′,wherein Q₄₁₁ and Q₄₁₂ may be hydrogen, deuterium, a C₁-C₂₀ alkyl group,a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, or a naphthyl group,

X₄₀₆ may be a single bond, O, or S,

R₄₀₁ and R₄₀₂ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, asubstituted or unsubstituted C₁-C₂₀ alkyl group, a substituted orunsubstituted C₁-C₂₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, and asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂),—B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁), —S(═O)₂(Q₄₀₁), and —P(═O)(Q₄₀₁)(Q₄₀₂), andQ₄₀₁ to Q₄₀₃ may each independently be selected from a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a C₆-C₂₀ aryl group, and a C₁-C₂₀heteroaryl group,

xc11 and xc12 may each independently be an integer from 0 to 10, and

* and *′ in Formula 402 each indicate a binding site to M in Formula401.

In one embodiment, A₄₀₁ and A₄₀₂ in Formula 402 may each independentlybe selected from a benzene group, a naphthalene group, a fluorene group,a spiro-bifluorene group, an indene group, a pyrrole group, a thiophenegroup, a furan group, an imidazole group, a pyrazole group, a thiazolegroup, an isothiazole group, an oxazole group, an isoxazole group, apyridine group, a pyrazine group, a pyrimidine group, a pyridazinegroup, a quinoline group, an isoquinoline group, a benzoquinoline group,a quinoxaline group, a quinazoline group, a carbazole group, abenzimidazole group, a benzofuran group, a benzothiophene group, anisobenzothiophene group, a benzoxazole group, an isobenzoxazole group, atriazole group, a tetrazole group, an oxadiazole group, a triazinegroup, a dibenzofuran group, and a dibenzothiophene group.

In one or more embodiments, in Formula 402, i) X₄₀₁ may be nitrogen andX₄₀₂ may be carbon, or ii) both X₄₀₁ and X₄₀₂ may be nitrogen(simultaneously).

In one or more embodiments, R₄₀₁ and R₄₀₂ in Formula 402 may eachindependently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a phenyl group, a naphthyl group, a cyclopentyl group,a cyclohexyl group, an adamantly group, a norbornanyl group, and anorbornenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantly group, anorbornanyl group, a norbornenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantly group, anorbornanyl group, a norbornenyl group a phenyl group, a biphenyl group,a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, atriazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, an adamantly group, a norbornanylgroup, a norbornenyl group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and adibenzothiophenyl group; and

—Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁),—S(═O)₂(Q₄₀₁), and —P(═O)(Q₄₀₁)(Q₄₀₂),

wherein Q₄₀₁ to Q₄₀₃ may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group,and a naphthyl group, but embodiments of the present disclosure are notlimited thereto.

In one or more embodiments, when xc1 in Formula 401 is 2 or more, twoA₄₀₁(s) in two or more L₄₀₁(s) may optionally be linked to each othervia X₄₀₇, which is a linking group, two A₄₀₂(s) may optionally be linkedto each other via X₄₀₈, which is a linking group (see Compounds PD1 toPD4 and PD7). X₄₀₇ and X₄₀₈ may each independently be a single bond,*—S—*′, *—C(═O)—*′, *—N(Q₄₁₃)-*′, *—C(Q₄₁₃)(Q₄₁₄)-*′, or*—C(Q₄₁₃)═C(Q₄₁₄)-*′ (wherein Q₄₁₃ and Q₄₁₄ may each independently behydrogen, deuterium, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, or a naphthyl group),but embodiments of the present disclosure are not limited thereto.

L₄₀₂ in Formula 401 may be a monovalent, divalent, or trivalent organicligand. In one or more embodiments, L₄₀₂ may be selected from halogen,diketone (for example, acetylacetonate), carboxylic acid (for example,picolinate), —C(═O), isonitrile, —CN, and phosphorus (for example,phosphine and/or phosphite), but embodiments of the present disclosureare not limited thereto.

In one or more embodiments, the phosphorescent dopant may be selectedfrom, for example, Compounds PD1 to PD25, but embodiments of the presentdisclosure are not limited thereto:

[Fluorescent Dopant in Emission Layer]

The fluorescent dopant may include the heterocyclic compound representedby Formula 1.

In addition, the fluorescent dopant may include an arylamine compound ora styrylamine compound.

The fluorescent dopant may include a compound represented by Formula501.

In Formula 501,

Ar₅₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

L₅₀₁ to L₅₀₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xd1 to xd3 may each independently be an integer from 0 to 3,

R₅₀₁ and R₅₀₂ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,and

xd4 may be an integer from 1 to 6.

In one embodiment, Ar₅₀₁ in Formula 501 may be selected from:

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup; and

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one embodiment, L₅₀₁ to L₅₀₃ in Formula 501 may each independently beselected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, and a pyridinylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, and a pyridinylene group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group.

In one or more embodiments, R₅₀₁ and R₅₀₂ in Formula 501 may eachindependently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃),

wherein Q₃₁ to Q₃₃ may be selected from a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and anaphthyl group.

In one or more embodiments, xd4 in Formula 501 may be 2, but embodimentsof the present disclosure are not limited thereto.

In one or more embodiments, the fluorescent dopant may be selected fromCompounds FD1 to FD22:

In one or more embodiments, the fluorescent dopant may be selected fromthe following compounds, but embodiments of the present disclosure arenot limited thereto.

[Electron Transport Region in Organic Layer 150]

The electron transport region may have i) a single-layered structureincluding (or consisting of) a single material, ii) a single-layeredstructure including (or consisting of) a plurality of differentmaterials, or iii) a multi-layered structure having a plurality oflayers consisting of a plurality of different materials.

The electron transport region may include at least one selected from abuffer layer, a hole blocking layer, an electron control layer, anelectron transport layer, and an electron injection layer, butembodiments of the present disclosure are not limited thereto.

In one or more embodiments, the electron transport region may have anelectron transport layer/electron injection layer structure, a holeblocking layer/electron transport layer/electron injection layerstructure, an electron control layer/electron transport layer/electroninjection layer structure, or a buffer layer/electron transportlayer/electron injection layer structure, wherein the constitutinglayers of each structure, are sequentially stacked from an emissionlayer. However, embodiments of the structure of the electron transportregion are not limited thereto.

The electron transport region (for example, a buffer layer, a holeblocking layer, an electron control layer, and/or an electron transportlayer in the electron transport region) may include a metal-freecompound containing at least one Tr-electron-deficientnitrogen-containing ring.

The term “7-electron-deficient nitrogen-containing ring” indicates aC₁-C₆₀ heterocyclic group having at least one *—N=*′ moiety as aring-forming moiety.

In one or more embodiments, the “7-electron-deficientnitrogen-containing ring” may be i) a 5-membered to 7-memberedheteromonocyclic group having at least one *—N=*′ moiety, ii) aheteropolycyclic group in which two or more 5-membered to 7-memberedheteromonocyclic groups, each having at least one *—N=*′ moiety, arecondensed with each other, or iii) a heteropolycyclic group in which atleast one 5-membered to 7-membered heteromonocyclic group, each havingat least one *—N=*′ moiety, is condensed with at least one C₅-C₆₀carbocyclic group.

Non-limiting examples of the π-electron-deficient nitrogen-containingring include an imidazole ring, a pyrazole ring, a thiazole ring, anisothiazole ring, an oxazole ring, an isoxazole ring, a pyridine ring, apyrazine ring, a pyrimidine ring, a pyridazine ring, an indazole ring, apurine ring, a quinoline ring, an isoquinoline ring, a benzoquinolinering, a phthalazine ring, a naphthyridine ring, a quinoxaline ring, aquinazoline ring, a cinnoline ring, a phenanthridine ring, an acridinering, a phenanthroline ring, a phenazine ring, a benzimidazole ring, anisobenzothiazole ring, a benzoxazole ring, an isobenzoxazole ring, atriazole ring, a tetrazole ring, an oxadiazole ring, a triazine ring, athiadiazole ring, an imidazopyridine ring, an imidazopyrimidine ring,and an azacarbazole ring.

In one or more embodiments, the electron transport region may include acompound represented by Formula 601:

[Ar₆₀₁]_(xe11)-[(L₆₀₁)_(xe1)-R₆₀₁])_(xe21)  <Formula 601>

In Formula 601,

Ar₆₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xe11 may be 1, 2, or 3,

L₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xe1 may be an integer from 0 to 5, and

R₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁),—S(═O)₂(Q₆₀₁), and —P(═O)(Q₆₀₁)(Q₆₀₂),

wherein Q₆₀₁ to Q₆₀₃ may each independently be a C₁-C₁₀ alkyl group, aC₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, or a naphthyl group, and

xe21 may be an integer from 1 to 5.

In one embodiment, at least one of the xe11 Ar₆₀₁(s) and the xe21R₆₀₁(s) may include the π-electron-deficient nitrogen-containing ring.

In one embodiment, ring Ar₆₀₁ in Formula 601 may be selected from:

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an isobenzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group; and

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an isobenzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group,—Si(Q₃₁)(Q₃₂)(Q₃₃), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

wherein Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group.

When xe11 in Formula 601 is 2 or more, two or more of Ar₆₀₁(s) may belinked to each other via a single bond.

In one embodiment, Ar₆₀₁ in Formula 601 may be an anthracene group.

In one or more embodiments, the compound represented by Formula 601 maybe represented by Formula 601-1:

In Formula 601-1,

X₆₁₄ may be N or C(R₆₁₄), X₆₁₅ may be N or C(R₆₁₅), X₆₁₆ may be N orC(R₆₁₆), and at least one of X₆₁₄ to X₆₁₆ may be N,

L₆₁₁ to L₆₁₃ may each independently be the same as described inconnection with L₆₀₁,

xe611 to xe613 may each independently be the same as described inconnection with xe1,

R₆₁₁ to R₆₁₃ may each independently be the same as described inconnection with R₆₀₁, and

R₆₁₄ to R₆₁₆ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group.

In one embodiment, L₆₀₁ and L₆₁₁ to L₆₁₃ in Formulae 601 and 601-1 mayeach independently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, and an azacarbazolyl group,

but embodiments of the present disclosure are not limited thereto.

In one embodiment, xe1 and xe611 to xe613 in Formulae 601 and 601-1 mayeach independently be 0, 1, or 2.

In one or more embodiments, R₆₀₁ and R₆₁₁ to R₆₁₃ in Formulae 601 and601-1 may each independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group;

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

—S(═O)₂(Q₆₀₁) and —P(═O)(Q₆₀₁)(Q₆₀₂),

wherein Q₆₀₁ and Q₆₀₂ are the same as described above.

The electron transport region may include at least one compound selectedfrom Compounds ET1 to ET36, but embodiments of the present disclosureare not limited thereto:

In one or more embodiments, the electron transport region may include atleast one compound selected from2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP),4,7-diphenyl-1,10-phenanthroline (Bphen), Alq₃, BAlq,3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole(TAZ), and NTAZ.

The thicknesses of the buffer layer, the hole blocking layer, and theelectron control layer may each independently be 20Å to about 1,000 Å,for example, about 30Å to about 300 Å. When the thicknesses of thebuffer layer, the hole blocking layer, and the electron control layerare within these ranges, excellent hole blocking characteristics and/orexcellent electron control characteristics may be obtained without asubstantial increase in driving voltage.

A thickness of the electron transport layer may be about 100Å to about1,000 Å, for example, about 150Å to about 500 Å. When the thickness ofthe electron transport layer is within the range described above,satisfactory electron transport characteristics may be obtained withouta substantial increase in driving voltage.

The electron transport region (for example, the electron transport layerin the electron transport region) may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include at least one selected from analkali metal complex and an alkaline earth-metal complex. A metal ion ofthe alkali metal complex may be selected from a lithium (Li) ion, asodium (Na) ion, a potassium (K) ion, a rubidium (Rb) ion, and a cesium(Cs) ion, and a metal ion of the alkaline earth-metal complex may beselected from a beryllium (Be) ion, a magnesium (Mg) ion, a calcium (Ca)ion, a strontium (Sr) ion, and a barium (Ba) ion. A ligand coordinatedwith the metal ion of the alkali metal complex or the alkalineearth-metal complex may be selected from a hydroxy quinoline, a hydroxyisoquinoline, a hydroxy benzoquinoline, a hydroxy acridine, a hydroxyphenanthridine, a hydroxy phenyloxazole, a hydroxy phenylthiazole, ahydroxy diphenyloxadiazole, a hydroxy diphenylthiadiazole, a hydroxyphenylpyridine, a hydroxy phenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, and acyclopentadiene, but embodiments of the present disclosure are notlimited thereto.

In one or more embodiments, the metal-containing material may include aLi complex. The Li complex may include, for example, Compound ET-D1(lithium quinolate, LiQ) or ET-D2:

The electron transport region may include an electron injection layerthat facilitates electron injection from the second electrode 190. Theelectron injection layer may directly contact the second electrode 190.

The electron injection layer may have i) a single-layered structureincluding (or consisting of) a single material, ii) a single-layeredstructure including (or consisting of) a plurality of differentmaterials, or iii) a multi-layered structure having a plurality oflayers consisting of a plurality of different materials.

The electron injection layer may include an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal compound, an alkalineearth-metal compound, a rare earth metal compound, an alkali metalcomplex, an alkaline earth-metal complex, a rare earth metal complex, orany combination thereof.

The alkali metal may be selected from Li, Na, K, Rb, and Cs. In oneembodiment, the alkali metal may be Li, Na, or Cs. In one embodiment,the alkali metal may be Li or Cs, but embodiments of the presentdisclosure are not limited thereto.

The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

The rare earth metal may be selected from scandium (Sc), yttrium (Y),cerium (Ce), terbium (Tb), ytterbium (Yb), and gadolinium (Gd).

The alkali metal compound, the alkaline earth-metal compound, and therare earth metal compound may be selected from oxides and halides (forexample, fluorides, chlorides, bromides, and/or iodides) of the alkalimetal, the alkaline earth metal, and the rare earth metal.

The alkali metal compound may be selected from alkali metal oxides (suchas Li₂O, Cs₂O, and/or K₂O), and alkali metal halides (such as LiF, NaF,CsF, KF, Lil, NaI, CsI, and/or KI). In one embodiment, the alkali metalcompound may be selected from LiF, Li₂O, NaF, Lil, NaI, CsI, and KI, butembodiments of the present disclosure are not limited thereto.

The alkaline earth-metal compound may be selected from alkalineearth-metal oxides (such as BaO, SrO, CaO, Ba_(x)Sr_(1-x)O (0<x<1),and/or Ba_(x)Ca_(1-x)O (0<x<1)). In one embodiment, the alkalineearth-metal compound may be selected from BaO, SrO, and CaO, butembodiments of the present disclosure are not limited thereto.

The rare earth metal compound may be selected from YbF₃, ScF₃, Sc₂O₃,Y₂O₃, Ce₂O₃, GdF₃, and TbF₃. In one embodiment, the rare earth metalcompound may be selected from YbF₃, ScF₃, TbF₃, YbI₃, ScI₃, and TbI₃,but embodiments of the present disclosure are not limited thereto.

The alkali metal complex, the alkaline earth-metal complex, and the rareearth metal complex may include ions of alkali metal, alkalineearth-metal, and rare earth metal as described above, and a ligandcoordinated with a metal ion of the alkali metal complex, the alkalineearth-metal complex, or the rare earth metal complex may be selectedfrom hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline,hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxyphenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazole,hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene,but embodiments of the present disclosure are not limited thereto.

The electron injection layer may include (or consist of) an alkalimetal, an alkaline earth metal, a rare earth metal, an alkali metalcompound, an alkaline earth-metal compound, a rare earth metal compound,an alkali metal complex, an alkaline earth-metal complex, a rare earthmetal complex, or any combination thereof, as described above. In one ormore embodiments, the electron injection layer may further include anorganic material. When the electron injection layer further includes anorganic material, the alkali metal, alkaline earth metal, rare earthmetal, alkali metal compound, alkaline earth-metal compound, rare earthmetal compound, alkali metal complex, alkaline earth-metal complex, rareearth metal complex, or combination thereof may be homogeneously ornon-homogeneously dispersed in a matrix including (or consisting of) theorganic material.

A thickness of the electron injection layer may be about 1Å to about 100Å, for example, about 3Å to about 90 Å. When the thickness of theelectron injection layer is within the range described above,satisfactory electron injection characteristics may be obtained withouta substantial increase in driving voltage.

[Second Electrode 190]

The second electrode 190 is located on the organic layer 150 having thestructure described above. The second electrode 190 may be a cathode,which is an electron injection electrode, and in this regard, a materialfor forming the second electrode 190 may be selected from a metal, analloy, an electrically conductive compound, and any combination thereof,each having a relatively low work function.

The second electrode 190 may include at least one selected from lithium(Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium(Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver(Mg—Ag), ITO, and IZO, but embodiments of the present disclosure are notlimited thereto. The second electrode 190 may be a transmissiveelectrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 190 may have a single-layered structure, or amulti-layered structure including two or more layers.

[Description of FIGS. 2 to 4]

An organic light-emitting device 20 according to FIG. 2 includes a firstcapping layer 210, a first electrode 110, an organic layer 150, and asecond electrode 190 sequentially stacked in this stated order; anorganic light-emitting device 30 according to FIG. 3 includes a firstelectrode 110, an organic layer 150, a second electrode 190, and asecond capping layer 220 sequentially stacked in this stated order; andan organic light-emitting device 40 according to FIG. 4 includes a firstcapping layer 210, a first electrode 110, an organic layer 150, a secondelectrode 190, and a second capping layer 220.

Regarding FIGS. 2 to 4, the first electrode 110, the organic layer 150,and the second electrode 190 may be understood by referring to thedescription presented in connection with FIG. 1.

In each of the organic light-emitting devices 20 and 40, light generatedin an emission layer of the organic layer 150 may pass through the firstelectrode 110 (which is a semi-transmissive electrode or a transmissiveelectrode), and the first capping layer 210 toward the outside, and inthe organic layer 150 of each of the organic light-emitting devices 30and 40, light generated in an emission layer may pass through the secondelectrode 190 (which is a semi-transmissive electrode or a transmissiveelectrode) and the second capping layer 220 toward the outside.

The first capping layer 210 and the second capping layer 220 mayincrease the external luminescent efficiency of the device according tothe principle of constructive interference.

The first capping layer 210 and the second capping layer 220 may eachindependently be an organic capping layer consisting of an organicmaterial, an inorganic capping layer consisting of an inorganicmaterial, or a composite capping layer including an organic material andan inorganic material.

At least one of the first capping layer 210 and the second capping layer220 may each independently include at least one material selected fromcarbocyclic compounds, heterocyclic compounds, amine-based compounds,porphyrin derivatives, phthalocyanine derivatives, naphthalocyaninederivatives, alkali metal complexes, and alkaline earth-metal complexes.The carbocyclic compound, the heterocyclic compound, and the amine-basedcompound may be optionally substituted with a substituent containing atleast one element selected from oxygen (O), nitrogen (N), sulfur (S),selenium (Se), silicon (Si), fluorine (F), chlorine (CI), bromine (Br),and iodine (I). In one embodiment, at least one of the first cappinglayer 210 and the second capping layer 220 may each independentlyinclude an amine-based compound.

In one embodiment, at least one of the first capping layer 210 and thesecond capping layer 220 may each independently include the compoundrepresented by Formula 201 or the compound represented by Formula 202.

In one or more embodiments, at least one of the first capping layer 210and the second capping layer 220 may each independently include acompound selected from Compounds HT28 to HT33 and Compounds CP1 to CP5,but embodiments of the present disclosure are not limited thereto:

The organic light-emitting device according to an embodiment has beendescribed in connection with FIGS. 1 to 4. However, embodiments of thepresent disclosure are not limited thereto.

The layers constituting the hole transport region, the emission layer,the layers constituting the electron transport region may be formed in aset or predetermined region using one or more suitable methods selectedfrom vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB)deposition, ink-jet printing, laser-printing, and laser-induced thermalimaging (LITI).

When the layers constituting the hole transport region, the emissionlayer, and the layers constituting the electron transport region areformed by vacuum deposition, the deposition may be performed at adeposition temperature of about 100° C. to about 500° C., a vacuumdegree of about 10⁻⁸ torr to about 10⁻³ torr, and a deposition speed ofabout 0.01 Å/sec to about 100 Å/sec, depending on the material to beincluded and the structure of the layer to be formed.

When the layers constituting the hole transport region, the emissionlayer, and the layers constituting the electron transport region areformed by spin coating, the spin coating may be performed at a coatingspeed of about 2,000 rpm to about 5,000 rpm and at a heat treatmenttemperature of about 80° C. to 200° C., depending on the material to beincluded and the structure of the layer to be formed.

[General Definition of Substituents]

The term “C₁-C₆₀ alkyl group” as used herein refers to a linear orbranched aliphatic hydrocarbon monovalent group having 1 to 60 carbonatoms, and examples thereof include a methyl group, an ethyl group, apropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group,a pentyl group, an isoamyl group, and a hexyl group. The term “C₁-C₆₀alkylene group” as used herein refers to a divalent group havingsubstantially the same structure as the C₁-C₆₀ alkyl group.

The term “C₂-C₆₀ alkenyl group” as used herein refers to a hydrocarbongroup having at least one carbon-carbon double bond in the middle or atthe terminus of the C₂-C₆₀ alkyl group, and examples thereof include anethenyl group, a propenyl group, and a butenyl group. The term “C₂-C₆₀alkenylene group” as used herein refers to a divalent group havingsubstantially the same structure as the C₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group” as used herein refers to a hydrocarbongroup having at least one carbon-carbon triple bond in the middle or atthe terminus of the C₂-C₆₀ alkyl group, and examples thereof include anethynyl group and a propynyl group. The term “C₂-C₆₀ alkynylene group”as used herein refers to a divalent group having substantially the samestructure as the C₂-C₆₀ alkynyl group.

The term “C₁-C₆₀ alkoxy group” as used herein refers to a monovalentgroup represented by —OA₁₀₁ (wherein A₁₀₁ is a C₁-C₆₀ alkyl group), andexamples thereof include a methoxy group, an ethoxy group, and anisopropyloxy group.

The term “C₃-C₁₀ cycloalkyl group” as used herein refers to a monovalentsaturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, andexamples thereof include a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term“C₃-C₁₀ cycloalkylene group” as used herein refers to a divalent grouphaving substantially the same structure as the C₃-C₁₀ cycloalkyl group.

The term “C₁-C₁₀ heterocycloalkyl group” as used herein refers to amonovalent monocyclic group having at least one heteroatom selected fromN, O, Si, P, and S as a ring-forming atom and 1 to 10 carbon atoms, andexamples thereof include a 1,2,3,4-oxatriazolidinyl group, atetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term“C₁-C₁₀ heterocycloalkylene group” as used herein refers to a divalentgroup having substantially the same structure as the C₁-C₁₀heterocycloalkyl group.

The term “C₃-C₁₀ cycloalkenyl group” as used herein refers to amonovalent monocyclic group that has 3 to 10 carbon atoms and at leastone carbon-carbon double bond in the ring thereof and no aromaticity,and examples thereof include a cyclopentenyl group, a cyclohexenylgroup, and a cycloheptenyl group. The term “C₃-C₁₀ cycloalkenylenegroup” as used herein refers to a divalent group having substantiallythe same structure as the C₃-C₁₀ cycloalkenyl group.

The term “C₁-C₁₀ heterocycloalkenyl group” as used herein refers to amonovalent monocyclic group that has at least one heteroatom selectedfrom N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms,and at least one carbon-carbon double bond in its ring. Examples of theC₁-C₁₀ heterocycloalkenyl group include a4,5-dihydro-1,2,3,4-oxatriazolylgroup, a 2,3-dihydrofuranyl group, and a2,3-dihydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkenylenegroup” as used herein refers to a divalent group having substantiallythe same structure as the C₁-C₁₀ heterocycloalkenyl group.

The term “C₆-C₆₀ aryl group” as used herein refers to a monovalent grouphaving a carbocyclic aromatic system having 6 to 60 carbon atoms, andthe term “C₆-C₆₀ arylene group” as used herein refers to a divalentgroup having a carbocyclic aromatic system having 6 to 60 carbon atoms.Examples of the C₆-C₆₀ aryl group include a phenyl group, a naphthylgroup, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, anda chrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀ arylenegroup each include two or more rings, the two or more rings may be fusedto each other.

The term “C₁-C₆₀ heteroaryl group” as used herein refers to a monovalentgroup having a heterocyclic aromatic system that has at least oneheteroatom selected from N, O, Si, P, and S as a ring-forming atom, inaddition to 1 to 60 carbon atoms. The term “C₁-C₆₀ heteroarylene group”as used herein refers to a divalent group having a heterocyclic aromaticsystem that has at least one heteroatom selected from N, O, Si, P, and Sas a ring-forming atom, in addition to 1 to 60 carbon atoms. Examples ofthe C₁-C₆₀ heteroaryl group include a pyridinyl group, a pyrimidinylgroup, a pyrazinyl group, a pyridazinyl group, a triazinyl group, aquinolinyl group, and an isoquinolinyl group. When the C₁-C₆₀ heteroarylgroup and the C₁-C₆₀ heteroarylene group each include two or more rings,the two or more rings may be condensed with each other.

The term “C₆-C₆₀ aryloxy group” as used herein refers to —OA₁₀₂ (whereinA₁₀₂ is a C₆-C₆₀ aryl group), and a C₆-C₆₀ arylthio group used hereinrefers to —SA₁₀₃ (wherein A₁₀₃ is a C₆-C₆₀ aryl group).

The term “C₁-C₆₀ heteroaryloxy group” as used herein refers to —OA₁₀₄(wherein A₁₀₄ is a C₁-C₆₀ heteroaryl group), and the term “C₁-C₆₀heteroarylthio group” as used herein refers to —SA₁₀₅ (wherein A₁₀₅ is aC₁-C₆₀ heteroaryl group).

The term “monovalent non-aromatic condensed polycyclic group” as usedherein refers to a monovalent group (for example, having 8 to 60 carbonatoms) having two or more rings condensed with each other, only carbonatoms as ring-forming atoms, and non-aromaticity in its entire molecularstructure. Examples of the monovalent non-aromatic condensed polycyclicgroup include a fluorenyl group. The term “divalent non-aromaticcondensed polycyclic group” as used herein refers to a divalent grouphaving substantially the same structure as the monovalent non-aromaticcondensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” asused herein refers to a monovalent group including two or more ringscondensed to each other, at least one heteroatom selected from N, O, Si,P, and S, in addition to carbon atoms (for example, 1 to 60 carbonatoms) as a ring-forming atom, and non-aromaticity in its entiremolecular structure. Examples of the monovalent non-aromatic condensedheteropolycyclic group include a carbazolyl group. The term “divalentnon-aromatic condensed heteropolycyclic group” as used herein refers toa divalent group having substantially the same structure as themonovalent non-aromatic condensed heteropolycyclic group.

The term “C₅-C₆₀ carbocyclic group” as used herein refers to amonocyclic or polycyclic group that includes only carbon as aring-forming atom and consists of 5 to 60 carbon atoms. The C₅-C₆₀carbocyclic group may be an aromatic carbocyclic group or a non-aromaticcarbocyclic group. The C₅-C₆₀ carbocyclic group may be a ring, such asbenzene, a monovalent group, such as a phenyl group, or a divalentgroup, such as a phenylene group. In one or more embodiments, dependingon the number of substituents connected to the C₅-C₆₀ carbocyclic group,the C₅-C₆₀ carbocyclic group may be a trivalent group or a quadrivalentgroup.

The term “C₁-C₆₀ heterocyclic group” as used herein refers to a grouphaving substantially the same structure as the C₅-C₆₀ carbocyclic group,except that as a ring-forming atom, at least one heteroatom selectedfrom N, O, Si, P, and S is used in addition to carbon (the number ofcarbon atoms may be in a range of 1 to 60).

In the present specification, at least one substituent of thesubstituted C₅-C₆₀ carbocyclic group, the substituted C₁-C₆₀heterocyclic group, the substituted C₃-C₁₀ cycloalkylene group, thesubstituted C₁-C₁₀ heterocycloalkylene group, the substituted C₃-C₁₀cycloalkenylene group, the substituted C₁-C₁₀ heterocycloalkenylenegroup, the substituted C₆-C₆₀ arylene group, the substituted C₁-C₆₀heteroarylene group, the substituted divalent non-aromatic condensedpolycyclic group, the substituted divalent non-aromatic condensedheteropolycyclic group, the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensedpolycyclic group, and the substituted monovalent non-aromatic condensedheteropolycyclic group may be selected from:

deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, anda C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆ oheteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆ o heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

wherein Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

The term “Ph” as used herein refers to a phenyl group, the term “Me” asused herein refers to a methyl group, the term “Et” as used hereinrefers to an ethyl group, the term “ter-Bu” or “But” as used hereinrefers to a tert-butyl group, and the term “OMe” as used herein refersto a methoxy group.

The term “biphenyl group” as used herein refers to “a phenyl groupsubstituted with a phenyl group”. In other words, the “biphenyl group”is “a substituted phenyl group” having “a C₆-C₆₀ aryl group” as asubstituent.

The term “terphenyl group” as used herein refers to “a phenyl groupsubstituted with a biphenyl group”. The “terphenyl group” is “asubstituted phenyl group” having “a C₆-C₆₀ aryl group substituted with aC₆-C₆₀ aryl group” as a substituent.

*, *′, and *″, as used herein, unless defined otherwise, each refer to abinding site to a neighboring atom in a corresponding formula.

Hereinafter, a compound according to embodiments and an organiclight-emitting device according to embodiments will be described in moredetail with reference to Synthesis Examples and Examples. The wording “Bwas used instead of A” used in describing Synthesis Examples indicatesthat an identical molar equivalent of B was used in place of A.

Synthesis Example Synthesis Example 1: Synthesis of Compound 1

2,6-diphenyl-9H-carbazole (1 eq), 2,6-difluorobenzonitrile (0.45 eq),and K₃PO₄ (2 eq) were dissolved in DMF and then stirred at 160° C. for12 hours. After cooling the mixture, the mixture was poured into a NaClaqueous solution to terminate the reaction, and further stirred for 30minutes. The resulting precipitate was filtered, extracted withdistilled water and DCM, dried over MgSO₄, and then dried under reducedpressure. An obtained organic layer (liquid) was purified by columnchromatography (MC/Hex) to thereby obtain Compound 1. (Yield: 65%)

Synthesis Example 2: Synthesis of Compound 60

(1) Synthesis of Intermediate 60-1

Intermediate 60-1 was synthesized in substantially the same manner asused to synthesize Compound 1, except that4-bromo-3,5-difluorobenzonitrile was used instead of2,6-difluorobenzonitrile. (Yield: 45%)

(2) Synthesis of Compound 60

Intermediate 60-1 (1 eq), (3,5-difluorophenyl)boronic acid (1 eq),Pd(PPh₃)₄ (5 mol %), and 4.15 g of K₂CO₃ (3 eq) were dissolved in aTHF/H₂O (2:1) mixed solution, and then stirred at 80° C. for 16 hours.The reaction solution was cooled to room temperature, and then extractedthree times with water and diethyl ether. An organic layer obtainedtherefrom was dried over magnesium sulfate, and a residue obtained byevaporation of a solvent was separated and purified by silica gel columnchromatography to thereby obtain Compound 60. (Yield: 33%)

Synthesis Example 3: Synthesis of Compound 61

(1) Synthesis of Intermediate 61-1

Intermediate 61-1 was synthesized in the substantially same manner asused to synthesize Compound 1, except that4-bromo-2,6-difluorobenzonitrile was used instead of2,6-difluorobenzonitrile. (Yield: 30%)

(2) Synthesis of Compound 61

Compound 61 was synthesized in substantially the same manner as used tosynthesize Compound 60, except that Intermediate 61-1 was used insteadof Intermediate 60-1. (Yield: 50%)

Synthesis Example 4: Synthesis of Compound 62

(1) Synthesis of Intermediate 62-1

Intermediate 62-1 was synthesized in substantially the same manner asused to synthesize Compound 1, except that4-bromo-2,6-difluorobenzonitrile was used instead of2,6-difluorobenzonitrile. (Yield: 50%)

(2) Synthesis of Compound 62

Compound 62 was synthesized in substantially the same manner as used tosynthesize Compound 60, except that Intermediate 62-1 was used insteadof Intermediate 60-1, and (2,6-difluorophenyl)boronic acid was usedinstead of (3,5-difluorophenyl)boronic acid. (Yield: 35%)

Synthesis Example 5: Synthesis of Compound 80

(1) Synthesis of Intermediate 80-1

Intermediate 80-1 was synthesized in substantially the same manner asused to synthesize Compound 1, except that 2,6-dimesityl-9H-carbazolewas used instead of 2,6-diphenyl-9H-carbazole, and1-bromo-3,5-difluorobenzene was used instead of2,6-difluorobenzonitrile. (Yield: 40%)

(2) Synthesis of Compound 80

Compound 80 was synthesized in substantially the same manner as used tosynthesize Compound 60, except that Intermediate 80-1 was used insteadof Intermediate 60-1, and (4-cyano-2,6-difluorophenyl)boronic acid wasused instead of (3,5-difluorophenyl)boronic acid. (Yield: 35%)

Synthesis Example 6: Synthesis of Compound 94

(1) Synthesis of Intermediate 94-1

Intermediate 94-1 was synthesized in substantially the same manner asused to synthesize Compound 1, except that2,6-di-tert-butyl-9H-carbazole was used instead of2,6-diphenyl-9H-carbazole, and 4-bromo-2,6-difluorobenzonitrile was usedinstead of 2,6-difluorobenzonitrile. (Yield: 43%)

(2) Synthesis of Compound 94

Compound 94 was synthesized in substantially the same manner as used tosynthesize Compound 62, except that Intermediate 94-1 was used insteadof Intermediate 62-1. (Yield: 25%)

Synthesis Example 7: Synthesis of Compound 109

(1) Synthesis of Intermediate 109-1

Intermediate 109-1 was synthesized in substantially the same manner asused to synthesize Intermediate 94-1, except that6-(tert-butyl)-2-phenyl-9H-carbazole was used instead of2,6-di-tert-butyl-9H-carbazole. (Yield: 40%)

(2) Synthesis of Compound 109

Compound 109 was synthesized in substantially the same manner as used tosynthesize Compound 60, except that Intermediate 109-1 was used insteadof Intermediate 60-1. (Yield: 36%)

Synthesis Example 8: Synthesis of Compound 113

Compound 113 was synthesized in substantially the same manner as used tosynthesize Compound 1, except that6,6′-difluoro-[1,1′-biphenyl]-3,3′-dicarbonitrile was used instead of2,6-difluorobenzonitrile. (Yield: 20%)

¹H NMR and MS/FAB of the compounds synthesized according to SynthesisExamples 1 to 9 are shown in Table 1 below.

Additional compounds other than the compounds shown in Table 1 may beeasily recognized by those skilled in the art by referring to the abovesynthesis routes and source materials.

TABLE 1 MS/FAB Compound ¹H NMR (CDCl₃, 400 MHz) found calc. 1 8.93-8.91(2H, m), 8.56-8.48 (6H, m), 8.40-8.35 (2H, m) 737.87 737.89 8.15-8.03(5H, m), 7.95-7.88 (8H, m), 7.71-7.53 (12H, m) 60 8.95-8.89 (2H, m),8.50-8.44 (8H, m), 8.39-34 (4H, m) 849.94 849.96 8.17-8.14 (2H, m),7.96-7.85 (8H, m), 7.70-7.54 (12H, m) 7.38-7.31 (1H, m) 61 8.96-8.91(2H, m), 8.58-8.45 (6H, m), 8.44-8.40 (2H, m) 849.95 849.96 8.22-8.01(6H, m), 7.96-7.89 (8H, m), 7.68-7.56 (12H, m) 7.50-7.45 (1H, m) 628.96-8.90 (2H, m), 8.58-8.47 (8H, m), 8.23-8.20 (4H, m) 849.94 849.967.96-7.89 (8H, m), 7.68-7.50 (15H, m) 80 8.49-8.27 (6H, m), 8.08-8.04(4H, m), 7.93-7.89 (2H, m) 1018.26 1018.28 7.75-7.66 (5H, m), 6.91-6.88(8H, m), 2.10-2.01 (36H, m) 94 8.49-8.26 (6H, m), 8.08-7.92 (4H, m),7.75-7.63 (5H, m) 769.1 770.0 6.91-6.80 (8H, m), 2.09-2.00 (36H, m) 1098.42-8.29 (6H, m), 8.06-7.96 (8H, m), 7.85-7.78 (4H, m) 809.96 809.987.66-7.50 (8H, m), 7.44-7.40 (1H, m), 1.72-1.66 (18H, s), 113 8.93-8.91(2H, m), 8.56-8.48 (6H, m), 8.40-8.35 (2H, m) 838.97 838.99 8.15-8.03(5H, m), 7.95-7.88 (8H, m), 7.71-7.53 (12H, m)

[Examples and Evaluation Examples] Evaluation of TADF CompoundCharacteristics

The compounds listed in Table 1 were respectively mixed in poly(methylmethacrylate) (PMMA) at a mass ratio of 9:1, and then dissolved indichloromethane to obtain a solution which was then spin-coated onquartz and then measured.

HOMO energy levels were measured by cyclic voltammetry (CV). LUMO energylevels were measured by calculating a difference of optical band gap atHOMO energy level. Triplet (T1) energy levels were measured from 77Kphotoluminescence (PL) spectra. Absolute photo-luminescence quantumyields (AbPLQY) were measured using a film doped with each compound at aconcentration of 10 wt % in PMMA. The measured results are shown inTable 2.

TABLE 2 PL λ_(max) HOMO LUMO AbPLQY ΔE_(ST) Compound [nm] [eV] [eV] [%](eV) 1 452 −5.925 −2.570 90 0.11 60 453 −6.038 −2.838 42 0.05 61 467−5.973 −2.950 87 0.06 62 454 −5.875 −2.762 94 0.06 80 456 −5.992 −2.86452 0.07 94 432 −5.799 −2.689 60 0.07 109 467 −5.949 −2.909 88 0.07 113451 −5.939 −2.715 95 0.18

Example 1

As an anode, a 15 Ωcm² (1,200 Å) ITO glass substrate available fromCorning Inc. was cut to a size of 50 mm×50 mm×0.7 mm, sonicated usingisopropyl alcohol and pure water for 5 minutes each, and then cleaned byirradiation of ultraviolet rays and ozone exposure for 30 minutes. Then,the resultant glass substrate was loaded onto a vacuum depositionapparatus. NPD was vacuum-deposited on the substrate to form a holeinjection layer having a thickness of 300 Å, and then TCTA as a holetransport compound was vacuum-deposited thereon to form a first holetransport layer having a thickness of 200 Å. CzSi as a hole transportcompound was vacuum-deposited on the first hole transport layer to forma second hole transport layer having a thickness of 100 Å. DPEPO andCompound 1 were co-deposited at a weight ratio of 90:10 on the secondhole transport layer to form an emission layer having a thickness of 200Å. Subsequently, DPEPO was deposited on the emission layer to form afirst electron transport layer having a thickness of 200 Å, and then,TPBI was deposited on the first electron transport layer to form asecond electron transport layer having a thickness of 300 Å.

LiF, which is a halogenated alkaline metal, was deposited on the secondelectron transport layer having a thickness of 10 Å, and then Al wasvacuum deposited to form a LiF/AI electrode (cathode electrode) having athickness of 3,000 Å, thereby completing manufacture of an organiclight-emitting device.

Examples 2 to 8 and Comparative Examples 1 to 3

Additional organic light-emitting devices were manufactured insubstantially the same manner as in Example 1, except that therespective Compounds described in Table 3 were used instead of Compound1 in forming an emission layer.

The organic light-emitting devices manufactured in Examples 1 to 8 andComparative Examples 1 to 3, were driven at a current density of 50mA/cm² and their performances were measured, and the results are shownin Table 1.

TABLE 3 Maximum Driving quantum Luminescent voltage EfficiencyEfficiency Emission material (V) (cd/A) (%) color Example 1  1 5.8 21.520   Blue Example 2  60 6.2 20.3 18.2 Blue Example 3  61 5.1 25.1 22.5Blue Example 4  62 5.3 26.2 24.1 Blue Example 5  80 5.2 23.3 21.6 BlueExample 6  94 5.0 25.5 23.9 Blue Example 7 109 5.2 24.8 23   BlueExample 8 113 5.7 20.9 19.3 Blue Comparative DPS 6.7 19.3 18.5 BlueExample 1 Comparative Compound 6.9 16.9 15.3 Deep Example 2 A blueComparative Compound 6.4 18.8 15.5 Bluish Example 3 B green <DPS>

<Compound A>

<Compound B>

As shown in Table 3, when a compound according to an embodiment of thepresent disclosure is used as a dopant in an emission layer, allExamples using the compound of the present disclosure showed excellentI-V-L characteristics including improved driving voltage and higherefficiency, compared to the organic light-emitting device of ComparativeExample 1 using DPS from the related art. In addition, it can beconfirmed that compared to Comparative Examples 2 and 3, driving voltageis improved and luminescence efficiency is excellent.

In other words, when the compound of the present disclosure is used as amaterial for an emission layer, the compound exhibits excellent effectsin terms of driving voltage, luminance, and efficiency.

Although the present disclosure has been described with reference to theSynthesis Examples and Examples, these examples are provided forillustrative purpose only, and one of ordinary skill in the art mayunderstand that these examples may have various modifications and otherexamples equivalent thereto. Accordingly, the scope of the presentdisclosure should be determined by the technical concept of the claims.

1. A heterocyclic compound represented by Formula 1:

wherein, in Formulae 1 and 2, A₁ is a C₅-C₆₀ carbocyclic group, a C₁-C₆₀heterocyclic group, a biphenyl group, or a terphenyl group, D₁ is agroup represented by Formula 2, n1 is an integer from 1 to 4, L₁ is asingle bond, a substituted or unsubstituted C₅-C₆₀ carbocyclic group, ora substituted or unsubstituted C₁-C₆₀ heterocyclic group, a1 is aninteger from 1 to 5, R₁, R₃, R₄, R₅, R₇, R₈, and Rug are eachindependently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryloxy group, asubstituted or unsubstituted C₁-C₆₀ heteroarylthio group, a substitutedor unsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂),—C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂), R₂ and R₆ are eachindependently selected from a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryloxy group, asubstituted or unsubstituted C₁-C₆₀ heteroarylthio group, a substitutedor unsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂),—C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂), wherein R₂ and R₆ are notsubstituted or unsubstituted carbazolyl groups, b11 is an integer from 0to 5, R_(w) is selected from: —F, a cyano group, and a C₁-C₂₀ alkylgroup substituted with at least one —F; a C₆-C₆₀ aryl group substitutedwith at least one selected from —F, a cyano group, and a C₁-C₂₀ alkylgroup substituted with at least one —F; a C₁-C₆₀ heteroaryl groupsubstituted with at least one selected from —F, a cyano group, and aC₁-C₂₀ alkyl group substituted with at least one —F; and a biphenylgroup and a terphenyl group, each substituted with at least one selectedfrom —F, a cyano group, and a C₁-C₂₀ alkyl group substituted with atleast one —F, b12 is an integer from 1 to 5, and at least onesubstituent of the substituted C₅-C₆₀ carbocyclic group, the substitutedC₁-C₆₀ heterocyclic group, the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted C₁-C₆₀ heteroaryloxy group, thesubstituted C₁-C₆₀ heteroarylthio group, the substituted monovalentnon-aromatic condensed polycyclic group, and the substituted monovalentnon-aromatic condensed heteropolycyclic group is selected from:deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group; a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂),—B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂); a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, and a monovalentnon-aromatic condensed heteropolycyclic group; a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group, each substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amidino group, a hydrazino group, a hydrazonogroup, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆ o alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂),—B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and —P(═O)(Q₂₁)(Q₂₂); and—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and wherein Q₁ to Q₃, Q₁₁ to Q₁₃,Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ are each independently selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group, and * indicates a binding site to aneighboring atom.
 2. The heterocyclic compound of claim 1, wherein n1 is2 or
 3. 3. The heterocyclic compound of claim 1, wherein n1 is 2 or 3,and D₁(s) in the number of n1 are identical to each other.
 4. Theheterocyclic compound of claim 1, wherein R₂ and R₆ are eachindependently selected from: a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxygroup; a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a cyanogroup, a phenyl group, and a biphenyl group; a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group,a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a perylenyl group, a pentacenyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, a silolyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolylgroup, an isoindolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, anisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, abenzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, abenzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, abenzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, atetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, and atriazinyl group; a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, abiphenyl group, a terphenyl group, a pentalenyl group, an indenyl group,a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a perylenyl group, apentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an indolyl group, an isoindolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, an isoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, aquinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, abenzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group,a triazolyl group, a tetrazolyl group, a thiadiazolyl group, anoxadiazolyl group, and a triazinyl group, each substituted with at leastone selected from deuterium, —F, —Cl, —Br, —I, a cyano group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, an indacenylgroup, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenylgroup, a furanyl group, a silolyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, abenzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinylgroup, a cinnolinyl group, a phenanthridinyl group, an acridinyl group,a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, a benzosilolyl group, abenzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, abenzoisoxazolyl group, a triazolyl group, a tetrazolyl group, athiadiazolyl group, an oxadiazolyl group, a triazinyl group,—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), and —B(Q₃₁)(Q₃₂); and —Si(Q₁)(Q₂)(Q₃),—N(Q₁)(Q₂), and —B(Q₁)(Q₂), and wherein Q₁ to Q₃ and Q₃₁ to Q₃₃ are eachindependently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.
 5. The heterocyclic compound of claim 1,wherein R₂ and R₆ are each independently selected from: a methyl group,an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group,an isobutyl group, a sec-butyl group, and a tert-butyl group; a methylgroup, an ethyl group, an n-propyl group, an isopropyl group, an n-butylgroup, an isobutyl group, a sec-butyl group, and a tert-butyl group,each substituted with at least one selected from deuterium, —F, —Cl,—Br, —I, and a cyano group; a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, and atriazinyl group; a phenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, and a triazinyl group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a cyano group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, a triazinyl group,—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), and —B(Q₃₁)(Q₃₂); and —Si(Q₁)(Q₂)(Q₃),—N(Q₁)(Q₂), and —B(Q₁)(Q₂), and wherein Q₁ to Q₃ and Q₃₁ to Q₃₃ are eachindependently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.
 6. The heterocyclic compound of claim 1,wherein each of R₃, R₄, R₅, R₇, and R₈ is hydrogen.
 7. The heterocycliccompound of claim 1, wherein R_(w) is selected from: —F, a cyano group,and a C₁-C₂₀ alkyl group substituted with at least one —F; and a phenylgroup, a biphenyl group, a terphenyl group, a pentalenyl group, anindenyl group, a naphthyl group, an azulenyl group, an indacenyl group,an acenaphthyl group, a fluorenyl group, a phenalenyl group, aphenanthrenyl group, a fluoranthenyl group, a triphenylenyl group, aperylenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an indolyl group, an isoindolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, an isoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, aquinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, aphenazinyl group, a benzofuranyl group, a benzothiophenyl group, abenzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, abenzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, atetrazolyl group, a thiadiazolyl group, and an oxadiazolyl group, eachsubstituted with at least one selected from —F, a cyano group, and aC₁-C₂₀ alkyl group substituted with at least one —F.
 8. The heterocycliccompound of claim 1, wherein R_(w) is selected from: —F, a cyano group,and —CF₃; and a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a pyridinyl group, a pyrazinyl group, and a pyrimidinylgroup, each substituted with at least one selected from —F, a cyanogroup, and —CF₃.
 9. The heterocyclic compound of claim 1, wherein R_(w)is a selected from —F, a cyano group, —CF₃, and groups represented byFormulae 5-1 to 5-7:

and wherein, in Formulae 5-1 to 5-7, * indicates a binding site to aneighboring atom.
 10. The heterocyclic compound of claim 1, wherein theheterocyclic compound is represented by any one of Formulae 1A-1 to 1A-4and 1B-1 to 1B-9:

and wherein, in Formulae 1A-1 to 1A-4 and 1B-1 to 1B-9, R₁₁ and R_(w)are the same as described in connection with Formula 1, R₁₂ and R₁₃ arethe same as described in connection with Ru in Formula 1, R_(wa) andR_(wb) are the same as described in connection with R_(w) in Formula 1,D_(1a) to D_(1c) are the same as described in connection with D₁ inFormula 1, b13 is 0, 1, 2, or 3, b14 is 1, 2, 3, or 4, and the sum ofb13 and b14 is 4, b15 is 0, 1, 2, or 3, b16 is 1, 2, 3, or 4, and thesum of b15 and b16 is 4, and b17 is 0, 1, or 2, b18 is 1, 2, or 3, andthe sum of b17 and b18 is
 3. 11. The heterocyclic compound of claim 1,wherein the heterocyclic compound is represented by any one of Formulae1A-2-1 to 1A-2-6, 1A-4-1, 1B-1-1 to 1B-1-2, 1B-4-1 to 1B-4-3, and 1B-7-1to 1B-7-3:

and wherein, in Formulae 1A-2-1 to 1A-2-6, 1A-4-1, 1B-1-1 to 1B-1-2,1B-4-1 to 1B-4-3, and 1B-7-1 to 1B-7-3, R₁₁ and R_(w) are the same asdescribed in connection with Formula 1, R₁₂ and R₁₃ are the same asdescribed in connection with Ru in Formula 1, R_(wa) to R_(wd) are thesame as described in connection with R_(w) in Formula 1, D_(1a) toD_(1c) are the same as described in connection with D₁ in Formula 1, b13is 0, 1, 2, or 3, and b17 is 0, 1, or
 2. 12. The heterocyclic compoundof claim 1, wherein the heterocyclic compound is represented by any oneof Formulae HA-2-1 to HA-2-6, HA-4-1, HB-1-1 to HB-1-2, HB-4-1 toHB-4-3, and HB-7-1 to HB-7-3:

and wherein, in Formulae HA-2-1 to HA-2-6, HA-4-1, HB-1-1 to HB-1-2,HB-4-1 to HB-4-3, and HB-7-1 to HB-7-3, R₁₁ and R_(w) are the same asdescribed in connection with Formula 1, R_(wa) to R_(wd) are the same asdescribed in connection with R_(w) in Formula 1, and D_(1a) to D_(1c)are the same as described in connection with D₁ in Formula
 1. 13. Theheterocyclic compound of claim 1, wherein the heterocyclic compound isselected from Compounds 1 to 126:


14. An organic light-emitting device comprising: a first electrode; asecond electrode facing the first electrode; and an organic layerbetween the first electrode and the second electrode and comprising anemission layer, wherein the organic light-emitting device comprises atleast one of the heterocyclic compound of claim
 1. 15. The organiclight-emitting device of claim 14, wherein the first electrode is ananode, the second electrode is a cathode, the organic layer furthercomprises a hole transport region between the first electrode and theemission layer and an electron transport region between the emissionlayer and the second electrode, the hole transport region comprises ahole injection layer, a hole transport layer, an emission auxiliarylayer, an electron blocking layer, or any combination thereof, and theelectron transport region comprises a hole blocking layer, an electrontransport layer, an electron injection layer, or any combinationthereof.
 16. The organic light-emitting device of claim 15, wherein thehole transport region comprises a hole transport layer, the holetransport layer comprises a first hole transport layer and a second holetransport layer, and a material included in the first hole transportlayer and a material included in the second hole transport layer areidentical to or different from each other.
 17. The organiclight-emitting device of claim 14, wherein the emission layer comprisesthe at least one heterocyclic compound.
 18. The organic light-emittingdevice of claim 14, wherein the emission layer comprises the at leastone heterocyclic compound and a host, and the at least one heterocycliccompound is a dopant.
 19. The organic light-emitting device of claim 17,wherein the heterocyclic compound included in the emission layer is athermally activated delayed fluorescence emitter (TADF emitter), and theemission layer is to emit delayed fluorescence.
 20. The organiclight-emitting device of claim 17, wherein the emission layer is to emitblue light having a maximum emission wavelength of 450 nm to 470 nm.